The Man Who Walked Backward

Ben Montgomery on Plennie Wingo’s attempt to walk backward around the world.

Jason Zasky May 20, 2019

When failed restauranteur Plennie Lawrence Wingo (1895-1993) decided to walk backward around the world, he had little to lose—at least from a financial perspective. After losing his Abilene, Texas café during the depths of the Great Depression, he turned to cooking at a greasy spoon, but struggled to earn enough to support his wife Della and daughter Vivian.

Convinced that a trek across the U.S.—and then Europe—would make him a wealthy man, he left his wife and child behind and departed Forth Worth, Texas, in April 1931 on a backward journey into the unknown. While Wingo earned media coverage at virtually every stop along his route, sponsors and endorsements never materialized and the nattily-dressed, coffee wood cane-carrying Texan was reduced to selling souvenir postcards as he walked.

“These were the worst hard times in American history,” offers Ben Montgomery, author of “The Man Who Walked Backward: An American Dreamer’s Search for Meaning in the Great Depression (Little, Brown/Spark). “Americans were riding the rails from town to town trying to find jobs. My own grandfather hitchhiked from Oklahoma to southern California to try to get work in an orchard or on a loading dock. Meanwhile, Plennie Wingo was out there walking backward, selling postcards,” quips the author.

In the following Failure Interview, Montgomery provides insight into the mind of a stubborn man who was remarkably persistent in the face of rejection. We also learn about some of the limited successes Wingo experienced, and how his round-the-world trip affected his marriage.

How did Plennie Wingo get the idea to walk around the world backward?

He came of age in the 1920s, which were full of characters doing all variety of stunts to try and achieve fame and fortune, including folks who would sit on flagpoles for hours on end. As these antics became more commonplace people started to look for weirder and weirder stunts. For example, there was a Texan [Bill Williams] who in 1929 pushed a peanut up [Colorado’s] Pikes Peak with his nose.

From all I can tell, Plennie Wingo was aware of these things and the idea to walk backward around the world just came to him. He was having a birthday party for his daughter and some boys were talking about how everything under the sun had been done. He said, “Not everything has been done. I never heard of anyone walking backward around the world.”

So he didn’t do a lot of thinking about it beforehand; he just wanted to get rich and famous by doing something nobody had done before. From that moment on he was obsessed with the idea.

So Wingo expected to succeed?

He thought he was going to become wealthy and believed everyone would be interested in funding his trip. Turns out times were so bad that nobody believed in his mission and hardly anyone was willing to give him money to promote their city or product. He also believed that when he got done he would write a book and that would make him a millionaire. To be sure, he got a ton of media attention; there were newspaper stories everywhere he went, but never the accompanying fortune.

So Wingo resorted to selling postcards to fund his travels?

Yeah, it was the only way he could make any money. And he was selling them at a pretty good clip. At first he didn’t know how much to charge. People would pull off the side of the highway and they would strike up a conversation [asking], “Why are you walking backward?”

He would explain what he was doing and say he had postcards for sale. They would say “How much?” And he’d say, “Whatever you want to pay.” He found some people would give a dollar and some would say they didn’t have any money and would take one for free. So finally he arrived at charging twenty-five cents per postcard and that was making him decent money—enough to get a bite to eat and a room wherever he went.

What did Wingo’s wife think of his idea to walk backward around the world?

She thought it was insane and idiotic and tried to discourage him from the first moment he brought it up. He promised her that this was his way to make it and support his wife and daughter. I think she thought he would see that he couldn’t make a go of it financially and would come back home. When he stayed out on the road and refused to come home she grew increasingly upset, to the point where her letters take a dire tone and she begins making demands: either you give up this cockamamie scheme and get a real job and start supporting us or you can expect to return home to nothing, nobody.

There is a moment in the book when he is flush with cash. He has just gotten a pretty decent gig advertising a medical product. The guy who hired him to do the advertising not only paid him but put him up for a couple nights. I tallied how much he had in his pocket and he had enough to send some money home to provide for his starving wife and daughter but he pocketed the money—he didn’t send anything home.

By the time he got to Rhode Island the divorce papers had caught up with him. But even under that kind of pressure he decided to keep going. He had already made it two-thousand miles at that point so he wasn’t about to stop. He signed the divorce papers, sent them back to Texas and pressed on.

Tell me about the practical challenges of walking backward.

Have you ever tried it? It is not an easy thing to do. First, you can’t see behind you. Wingo serendipitously stumbled across an advertisement in a magazine for a pair of glasses that had little rear-view mirrors affixed to the sides. And he got good about navigating obstacles. In fact there is footage of him on YouTube that shows him walking backward through Chicago and he’s navigating packed sidewalks and intersections and climbing stairs.

You mentioned that Wingo got a lot of publicity—a lot of advance publicity. Did he encounter any problems from people who knew he was coming?

He had his share of run-ins with the law. Because of the number of migrants during the Great Depression a lot of municipalities had ordinances and local laws to prohibit panhandling and begging for money. There were a lot of traveling folk out looking for work—and a lot of homeless families going from place to place—so cities tried to discourage people from setting up on street corners and begging for food or money.

When officers of the law would see Wingo walking around town wearing a sign that said “Around the World Backward,” well, he had the appearance of a hobo sometimes, even though he was wearing his best clothes. They would harass him and tell him to leave town, mistaking him for a vagabond. He would plead his case and tell them he wasn’t begging for money—that he was selling postcards and not taking or expecting charity. A lot of times the police would let him go; occasionally he’d have to appeal to the mayor or police chief and the police would back off. But a couple of times he spent a night or two in jail.

Are you surprised Wingo wasn’t more successful from a financial perspective?

With the kind of attention he was getting … almost every town he walked into, there was, at a minimum, a newspaper article about him and a photograph. That kind of thing was interesting in 1931—it might still be interesting today. So it does surprise me that hardly anyone took him up on his offer to represent their company. But it was the 1930s and things were really bad and no one knew what the future held.

Wingo certainly seems to have been persistent in the face of rejection.

Everywhere he went he tried [to get sponsorship] but he struck out time and time again. He thought he was going to make bank on his trip and that all his desires would be met but that didn’t happen. He thought everyone would buy his book but it did not sell well. What it got him was an appearance on The Tonight Show starring Johnny Carson [on July 13, 1976] and they paid him like $350. It also got him a small gig advertising a new Ripley’s Believe it or Not Museum in [Santa Monica] California.

But while he didn’t profit financially he got a lot of mileage from telling the story. There weren’t a whole lot of people able to travel and see the world during the Great Depression. He saw a lot of the country and made it to Europe—walking from Hamburg to Istanbul—despite leaving Texas without a penny to his name. That’s a remarkable achievement, even if he did come home with only four dollars in his pocket.